32 Whiskey Cocktails to Warm Your Soul This Fall and Winter

Nothing is more soul-warming than curling up by the fireplace with a hot toddy or spiked eggnog in hand, and it’s all thanks to whiskey. If your experience with the spirit starts and ends with a Jack and Coke, it’s high time you branched out. Whiskey’s signature oaky flavor pairs beautifully with everything from apple cider to hot cocoa. There are also a range of varieties to explore, like sweet bourbon and peppery rye. Whiskey also pairs well with tart produce and sour beverages, like blackberries and lemonade, so you can sip it during the summertime too. Read on for 32 whiskey cocktails to shake up at home all year round.

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1. Slow Cooker Cranberry Hot Toddy

  • Time Commitment: 4 hours and 5 minutes

This soothing sipper is like the cashmere sweater of cocktails, thanks to cranberry juice, fresh tangerines, ginger and warm spices. The big-batch recipe calls for amber rum and brandy, but feel free to substitute the former with traditional bourbon.

2. Classic Eggnog

  • Time Commitment: 1 hour and 35 minutes

This creamy, cinnamon-y, nutmeg-kissed bev pairs well with dark rum, brandy and Cognac alike, but bourbon is our go-to choice. Be sure to leave a glass out for Santa.

3. Blood Orange Bourbon Sour

  • Time Commitment: 5 minutes

For the record, bourbon is a type of whiskey that’s mash is made up of at least 51 percent corn. It must be distilled and aged in charred oak barrels, typically resulting in a sweeter, more nuanced flavor with notes of caramel and vanilla. (That also makes it a delicious pairing for citrus.)

4. Chai Hot Toddy

  • Time Commitment: 15 minutes

Using chai tea instead of black makes this drink super autumnal. Serve it with whiskey, spiced rum or even Baileys.

5. Spiced Honey Bourbon Old Fashioned

  • Time Commitment: 15 minutes (plus cooling time)

Instead of simply muddling an orange slice and maraschino cherry, this drink gets an ounce of fresh clementine juice, orange bitters and spiced rosemary-honey syrup.

6. Classic Manhattan Cocktail

  • Time Commitment: 5 minutes

Rye is the star of this old-school cocktail, dashed with two types of bitters and sweet vermouth.

7. Blueberry Whiskey Buck

  • Time Commitment: 5 minutes

The drink is topped with ginger beer, so it’s equal parts sweet, sour and spicy. Use fresh blueberries when they’re in season and substitute frozen when they aren’t.

8. Honeycrisp and Bourbon Spiced Cider

  • Time Commitment: 15 minutes

There’s no shortage of fall spices in this fruity libation. We’re talking whole cloves, cardamom pods, star anise and cinnamon sticks.

9. Holiday Cheermeister Bourbon Punch

  • Time Commitment: 10 minutes

Whip this up for your guests and you’ll land a permanent spot on their nice list. Pomegranate juice and fresh-squeezed OJ offer acidity, while prosecco turns the cocktail bubbly.

10. Hot Buttered Bourbon

  • Time Commitment: 30 minutes

Just as decadent as its rum-laced predecessor. The base is a rich concoction of butter, brown sugar, maple syrup and spices. Once it’s cooked, all it needs is hot water and a few shots of bourbon.

11. Whiskey Lemonade

  • Time Commitment: 5 minutes

You’re only three ingredients away from this summer thirst-quencher. Use store-bought lemonade to save time or make your own (and infuse it with herbs like lavender and rosemary).

12. Garden Cherry Bourbon Smash

  • Time Commitment: 5 minutes

Fresh or frozen cherries work here—just be sure to spring for fresh basil and thyme. Don’t even get us started on the herby ginger-sugar rim.

13. Cinnamon Maple Whiskey Sour

  • Time Commitment: 5 minutes

Tastes just like a fall evening spent by the bonfire, wrapped in your favorite quilt. We feel a spooky movie marathon coming on.

14. Maple Ginger Hot Toddy

  • Time Commitment: 10 minutes

Did you know the hot toddy is often used as a cold remedy? Give this one a try next time you have the sniffles, since it’s loaded with freshly muddled ginger. (While mostly anecdotal, some believe it can boost your immune system. Other research suggests ginger can help you feel less nauseous.)

15. Spiced Bourbon Punch

  • Time Commitment: 20 minutes

No one likes to play bartender at their own party. So, stir this mix of bourbon, Champagne, apple cider and spiced simple syrup in a big punch bowl and let your guests serve themselves.

16. Caramel Apple Old Fashioned

  • Time Commitment: 30 minutes

Homemade cider caramel takes this bev over the top. Better yet, it comes together in just a few minutes. Muster all the patience you can while waiting for it to cool.

17. Maple Pumpkin Steamed Almond Milk with Bourbon

  • Time Commitment: 10 minutes

She’s gluten-free, dairy-free and oh so autumnal, down to the pumpkin pie spice-dusted whipped cream crown. (BTW, if you don’t have any premixed pumpkin pie spice, you can easily make your own.)

18. Bourbon Ginger Cider Cocktails

  • Time Commitment: 10 minutes

Ginger beer + apple cider = the ultimate fall combo. We’re even betting you can turn this libation into a float by finishing your glass with a scoop of vanilla ice cream.

19. Cinnamon Bourbon Old Fashioned with Brûléed Oranges

  • Time Commitment: 10 minutes

This version of the O.G. cocktail isn’t as boozy as the original, but once you taste the homemade maple-cinnamon simple syrup, you won’t mind one bit.

20. Blackberry Lemonade

  • Time Commitment: 40 minutes

Spike it with blackberry whiskey, bourbon, silver rum or lemon vodka—the bar cart is your oyster.

21. Cinnamon Cider Whiskey Sour

  • Time Commitment: 30 minutes

Garnish these sweet-tart sippers with apple slices, lemon wedges or cinnamon sticks. Bonus points for slicing the apples with a leaf-shaped cookie cutter.

22. Pumpkin Eggnog

  • Time Commitment: 2 hours and 5 minutes (including chill time)

Sure, you could just infuse store-bought nog with pumpkin purée and spices. But it’ll be a million times more satisfying if you make it from scratch.

23. Citrus Whiskey Tea Punch

  • Time Commitment: 35 minutes

Complete with pomegranate-lemon ice cubes. Whiskey and applejack, a liquor made from apple brandy and grain alcohol that’s known as America’s first spirit, unite to make this crowd-pleaser possible.

24. Cranberry Bourbon Sour

  • Time Commitment: 15 minutes

Be sure to use 100 percent cranberry juice instead of cranberry juice cocktail: Its flavor is much more intensely tart and better complements this drink.

25. New York Whiskey Sour

  • Time Commitment: 5 minutes

This classic cocktail sports a signature red wine float. Pick a vino that’s full-bodied, like Cabernet Sauvignon or Syrah.

26. Irish Whiskey Smash

  • Time Commitment: 5 minutes

Think of it as a citrusy riff on the mint julep. Be gentle with the mint as you muddle it, so its flavorful oils are released without the leaves getting shredded.

27. Berry Naughty

  • Time Commitment: 20 minutes

Complete with a charcoal-dusted lump of "coal" (aka a prune) for a garnish. Punchy rye is simultaneously brightened by winter citrus and cranberry and softened by a duo of liqueurs.

28. Apple Cider Sangria

  • Time Commitment: 20 minutes

It's just the crowd-pleaser to kick off Thanksgiving cocktail hour (or a Halloween party). Apple cider's sweet-tart flavor is a great pairing for maple whiskey and white wine.

29. The Man O’ War Cocktail

  • Time Commitment: 5 minutes

Bourbon or rye work well in this throwback bev (which is named after a famous horse from the 1920s)—just be sure to use freshly squeezed lemon juice, not bottled.

30. A Long Winter’s Nap

  • Time Commitment: 20 minutes

Consider this soothing sipper a liquid lullaby. Save the leftover spice-infused maple syrup for a bold twist on waffles or French toast.

31. Iced Whiskey Coffees with Whiskey Syrup and Whipped Cream

  • Time Commitment: 35 minutes

We can't decide what we're more obsessed with, the light-as-air coconut whipped cream or the brown sugar-whiskey syrup (which we're betting tastes divine over pecan pie and vanilla ice cream).

32. Bourbon Spiked Hot Chocolate

  • Time Commitment: 10 minutes

Packet hot cocoa doesn’t even compare to this homemade version, made with cocoa powder, vanilla and semi-sweet chocolate. Trust.

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Taryn Pire is PureWow’s associate food editor. A former bartender and barista, she’s been writing about all things delicious since 2016, developing recipes, reviewing restaurants and investigating food trends at Food52, New Jersey Family Magazine and Taste Talks. When she isn’t testing TikTok’s latest viral recipe, she’s having popcorn for dinner and posting about it on Instagram @cookingwithpire.